


Truth or Dare -- Slave Sam/Master Dean

by dawnoftheagez



Category: Supernatural
Genre: Anal Fingering, Anal Gaping, Anal Play, Anal Plug, Anal Sex, Anal Virgin Sam Winchester, Begging, Begging Sam Winchester, Bottom Sam, Chains, Cock Slapping, Cock Slut, Cock Slut Sam Winchester, Cock Sucking, Collar, Come Swallowing, Dean Winchester Owns Sam Winchester, Dean fucks Sam, Deans Cum, Dildo play, Dildos, Dominate Dean Winchester, Fingerfucking, Gagball, Large Cock, Leashes, M/M, Master Dean, Master Dean Winchester, Master Dean/Slave Sam Winchester - Freeform, Master/Slave, Naked Dean Winchester, Naked Sam Winchester, Name-Calling, Sam is Dean's Slave, Sam is Filled with Deans Cum, Sams cum, Slave Sam, Slave Sam Winchester, Spanking, Submissive Sam Winchester, Talk of rules, Top Dean Winchester, Truth or Dare, Whipping, Wincest - Freeform, Wincest fuck, ballgag, beg, cockring, filled with cum, master - Freeform, mouth fucked, naked, sir, slut, whip
Language: English
Status: Completed
Published: 2019-06-16
Updated: 2019-08-21
Packaged: 2020-05-12 23:17:17
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,169
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19239115
Author URL: https://archiveofourown.org/users/dawnoftheagez/pseuds/dawnoftheagez
Summary: Slave Sam / Master Dean --Truth or Dare --- Its been to long since Dean had any fun, and realizing his feelings for his brother Dean decided to act on it. During a game of truth or dare Dean manages to coax it out of his brother that he has feelings too, and than the toys, and the chains come out. -





	1. Truth or Dare

"Sam, I am bored."

Sam chuckled as he ate his salad, reading a book on some recent hunts and making sure he had the information written down.

"Can we play a game?"

"What kind of game?" Sam asked lifting an eyebrow. He closed the book looking to his brother, Dean smirked. "Like a card game, a board game? We don't have any video games, that I know of."

"Truth or Dare, and we have to be 100% honest!" He said sitting across from his brother. He needed to know the truth, and he was going to get it, and have fun while doing it.

"Alright, why not." He pushed his books over and set his salad out of the way. "You go first?"

"As always, I am older." Dean said booping his brothers nose. Sam scrunched it confused at the action. "Alright, truth or dare?"

"Truth." 

"Boring, uhm.. what do you dream about before bed?"

Sam thought for a moment. "Usually nothing, or its a nightmare, or the people we have lost."

"Thats depressing."

"You said 100% honest." Sam reminded. "What do you dream about?"

"Burgers." Dean said holding his hands out to show an invisible burger. "Juicy ass burgers." He took a fake bite and Sam laughed. 

"Truth or Dare."

"Dare."

"I dare you to run around the bunker. Naked."

Sam looked at his brother. "Are you serious?" 

"Dead serious, come on clothes off." 

"Fine." Sam pouted and got his shirt off first, Dean's pants grew tight. He than dropped his pants and his boxers, his large cock springing out. He looked to his brother than headed off, running around the bunker. Dean smiled watching. He returned. "Can I put these back on now?"

"No, keep em off."

"Why..why?"

"Part of the dare. My turn, I choose truth."

"Why did you have me take them off?"

"Fun of it. Truth or Dare?"

"Truth." He said fidgeting. 

"Do you like me, in a..sexual way?" Dean asked grabbing for his brothers cock under the table. Sam let out a gasp as he began to pump his thick member. 

"Yes..yes Dean..I have for a long..long time." He moaned. "Truth or Dare, brother?"

"Truth."

"Do you like me in a sexual way?"

"No shit." Dean said back."Truth or Dare."

"Truth."

"Will you honestly be my slave? Call me master, do as I ask?"

"Yes..yes sir." Sam moaned. "Truth or-"

"No, lay on the table. Cock up." He snapped. "I will be back." Sam let out a fast breath, what was he getting himself into? Soon Dean was back and he had a few items in hand. A collar, leash, dildos, ball gags. A cock-ring, flogger, whip. Chains. 

"Dean. I..what are you." Dean took the whip and hit him across the chest. "Oww."

"Master!" Dean snapped, becoming more dominate. "Master, or sir. Do you understand me?" He asked grabbing his hair in his fist and pulling him closer. 

"Yes..yes sir." Sam whined, his cock already throbbing. 

"Good." Dean snarled as he took off his clothes, his cock large as well. "Turn around ass up." Sam didn't hesitate, his ass was up in the air and his face was pressed against the table. He felt his cock throbbing, soon a cock-ring was around the base. He was collared and Dean slipped a chain around it instead of a leash and chained his neck down on the table. "Sexy sexy slut." He said as he pinched a nipple. He let out a moan and opened his mouth to speak when the gag-ball was inserted, saliva began to pool around it, dripping. 

"Are you an anal virgin Sammy?"

The man began to nod his head up and down. A muffled "yes sir." could be heard through the gag. Dean smiled and got on his knees behind him, he put a little lube on his fingers and began to slowly insert one. Sam twitched and began to moan at the new sensation. His ass was being spread out, Dean soon had two in and was slowly fucking it. Sam was moaning loudly into the ball, and precum was dripping from his swollen cock, the ring keeping him from really letting go. 

"Such a slut for me Sam." Sam nodded his head and than let out a shout as a third finger was in, after ten agonizing minutes Dean had his entire fist in his ass. He wasn't relenting. "You can cum bitch." Dean said as he removed the cock ring. Dean was ready to insert his own cock, but wanted to play. He fisted his brothers ass until the table was covered in sticky white hot cum. "Such a slut." Dean stated again as he began to pump his brothers thick cock with his other free hand. Sam was gripping the table, soon Dean pulled his fist out and inserted a large dildo to keep it stretched. He handcuffed his hands together under the table, and found a ankle spreader and chained his legs together. "I bet you are wondering where all these toys came from huh Sam?" He asked as he removed the gag for a moment.

"Yes..yes master." Sam moaned, Dean smirked and began to rub his cock along Sam's face never coming close to his mouth, but Sam tried to lick it non the less. "Master please tell me sir."

"I have been planning to fuck your tight holes for.." He thought about it. "Since we started hunting together. I have been wanting to fill that ass with my cum, and hear you beg for me to never stop. I have wanted to hear you scream my name, and call me master. I have wanted to do this for such a long long time." Dean sand as he grabbed the boys hair, and slammed his cock into the back of his mouth. His tip hit the back of his throat and he gagged but Dean just kept fucking, soon his mouth was filled with his brothers cum. Dean smiled and pulled his cock out, Sam swallowed what he could while more dripped onto the table and the floor. Dean slapped his brothers mouth with his cock than returned to his gapping ass. Dean pulled out the toy and replaced it with his cock. 

Sam moaned, screaming slightly as Dean began to move. "Don't stop begging." Dean growled. "Beg, moan, scream even, but you cannot cum till you master gives you the okay."

"Yes master." Sammy moaned, it was a strange, and yet intoxicating feeling. His brothers cock filled his ass. Dean wasn't soft either. He had his cock as far as he could go, his balls pressing against his skin. He began to move slower, but deeper and Sam's eyes were rolled back, his mouth open, moans escaping his lips. "Master... master please faster..please sir." He begged. Dean smiled, and didn't adjust himself before he began to go as quickly as he could. His tip pressing against Sam's g-spot. "MASTER!" Sam screamed, his cock throbbing, needing to cum. "I need to cum..please please sir please please!" He begged. Dean smiled and stopped holding his cock deep. "Please..pl..please. Master."

"After I do." Dean snapped slapping his brothers ass, Sam let out a yelp and moved causing Dean to ram into his sensitive spot again. A red handprint soon appeared, and Dean continued. "Got it slut?"

"Yes. Yes sir. OH god...SIR!" He moaned as he felt his cock ready to cum again. Dean soon released his load into his brothers throbbing ass. He smiled filling him up completely, more split out around his cock.

"Go on bitch, cum for your master." Dean snapped as he pulled out of his brother, and put the toy back inside to keep the cum in. Sam began to cum, the table pooled with his sperm. His knee was sticky and the table was going to need to be cleaned. Dean smiled and looked through the toy chest. "What a good slut, already pleasing your master so well. I have some rules now that I am your master. On hunts, unless in a hotel room, you can call me by my name. When we have friends or guests I am Dean, any other time you call me Master, Sir, or Master Dean. You will wear that pretty collar around your neck 80% of the day, no masterbating, no coming without permission. You do as I ask whenever I ask. You are my cum bucket, I will fill you when I please. You will ask for it when you want sex, but I will not always permit. You will wear a buttplug and be naked around the house, your room is now our playroom, you will sleep in my bed or on the floor of my room. You ask permission to do things. You get to eat my cum for breakfast with oatmeal and when I ask for it you do whatever I say got it Sammy?"

"Yes..yes master. Master Dean I will do any and all things you ask of me. Sir."

"Good little whore." He said as he pulled out the dildo and stuck his cock back in. "Round two."


	2. Sam knows how to treat his master

**Summary for the Chapter:**

> chapter 2 of 2
> 
> please know i take story requests! I would love to know what yall wanna see Fluffy or NSFW

Sam let out a frown as he waited for Dean to return from the store, he was tied to a chair naked, his ass was filled with an anal toy, his cock twitching as he adjusted himself in the chair. He wanted his master to allow him to cum, he needed him to. He heard the door open and he began to jump in the chair, the anal toy hitting his prostate. He let out a cry as he felt him grow close to cumming once again. He knew that Dean would punish him if he did so he took all his power not to cum. He let out a scream as he waited for Dean to come to him. 

Dean made his way down to his brother, a smirk on his face. "You did so well pet. Go on and cum." 

Sam quickly did, thanking Dean with each squirt of his cock. "Master please.. may I be used to pleasure you?" Sam begged. Dean smiled and untied him, he dropped to his knees and the toy was forced back into his ass. 

"Suck my cock, now."

Sam nodded and began to bob his head sucking his cock quickly. He licked up and down his shaft, sucking his balls and tip. Dean groaned as he forced his cock down his brothers throat. Dean smiled as Sam began gagging. Dean let himself cum, he filled the boys mouth, and waited for him to swallow to begin again. Sam sucked quickly, he didn't want to let down his master, he wanted to give him everything. 

"Master please, fill me." Sam begged. 

Dean enjoyed that he was the master. He made him crawl following behind him, the toy in his ass was as deep as it could be. Sam was hardly moving, but he was moving. He knew his master would be angry if he stopped. Finally they came to the playroom. "Stand up slut."

Sam nodded and stood up quickly, and Dean bent him over the slotted table. He popped the toy out and quickly inserted his own cock fucking him hard and fast. His balls slapping against his skin, he spanked his ass and pulled his hair. Sam let out a scream as Dean bucked his hip quickly forcing his cock deep into his ass, he let out a grunt as he ejaculated into his ass. Sam let out another scream as Dean forced his cock deeper inside. Sam panted as Dean pulled out slowly, and then began to force himself back inside. 

Sam was panting, his cock twitching. "May I please cum sir, please please sir."

"Wait." Dean ordered, Sam panted but nodded understanding what he was told to do. Dean smirked and began to slowly insert his cock in and out of his quivering ass. 

"Master...sir please!" He begged again. "I really want to cum, please sir!" 

He began to scream as Dean slapped his ass again. "Go ahead." 

Sam came, his jizz covering the table under him in a sticky mess. 

Dean smiled as he bit his shoulder and squeezed his sides as he began to quickly fuck him. He wanted to fill him as deep as he could. He let out a scream as Dean pulled out slapped his ass and forced his cock deep in. Sam found that his cock was throbbing again. He felt his masters cock doing the same, throbbing deep in his ass. 

Dean pulled out and inserted a cock toy in his ass. He walked around the table and began to fuck his mouth. Sam swallowed each one of his ejaculations. His seed dripped from his mouth. 

Dean smiled as he spanked him leaving him bent over the table. "I will be back in like.. say an hour I am going to make some pie."

**Author's Note:**

> Hope you liked it!  
> I do take requests!  
> Please feel free to ask more more chapters, or other books!


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